5-Hexenoyl chloride → Hex-5-enoic acid (6-methoxy-[1,5]naphthyridin-4-yl)-amide

HRID 1640517Notes

Reaction equation

HRID 1640517 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH2:13].[C:14](Cl)(=[O:20])[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19]>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH:13][C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19]

Participants

4

Reactant 2

HCID 109755195-Hexenoyl chlorideHCID 114352366-Methoxy-1,5-naphthyridin-4-amine

Product 1

HCID 66736318Hex-5-enoic acid (6-methoxy-[1,5]naphthyridin-4-yl)-amideYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 6-methoxy-[1,5]naphthyridin-4-ylamine (1.5 g, 8.56 mmol) and TEA (1.55 mL, 1.3 eq.) in DCM (8.5 mL) was added 5-hexenoyl chloride (1.36 g, 1.2 eq.) in DCM (1.5 mL) at rt. The resulting suspension was vigorously stirred at rt for 20 h. The mixture was then washed with water. The org. layer was dried over Na2SO4 and concentrated. The residue was chromatographed on SiO2 (DCM-MeOH—NH4OH: 1000:50:4) to afford the title intermediate as a yellow solid (1.66 g, 71% yield).

Workup

  1. washThe mixture was then washed with water
  2. dry with materiallayer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed on SiO2 (DCM-MeOH—NH4OH: 1000:50:4)

Sources & evidence

ORD record
ord-341c6b4efe8b4d9ba1c6f039173bc119
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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